134977-99-4Relevant academic research and scientific papers
Access to C5-Alkylated Indolines/Indoles via Michael-Type Friedel-Crafts Alkylation Using Aryl-Nitroolefins
Ertugrul, Berrak,Kilic, Haydar,Lafzi, Farrokh,Saracoglu, Nurullah
, p. 9018 - 9038 (2018/06/27)
A straightforward synthetic route toward C5-alkylated indolines/indoles has been developed. The strategy is composed of Zn(OTf)2-catalyzed Friedel-Crafts alkylation of N-benzylindolines with nitroolefins, and a series of diverse indolines was first obtained in up to 99% yield. This reaction provides a direct and practical route to a variety of the C5-alkylated indolines which were also utilized for accessing corresponding indoles. Indoline derivatives with free NH groups could be obtained through an N-deprotection reaction. Moreover, the primary alkyl nitro groups in both indolines and indoles are amenable to further synthetic elaborations, thereby broadening the diversity of the products.
Palladium-catalyzed Suzuki-Miyaura coupling of amides by carbon-nitrogen cleavage: General strategy for amide N-C bond activation
Meng, Guangrong,Szostak, Michal
, p. 5690 - 5707 (2016/07/06)
The first palladium-catalyzed Suzuki-Miyaura cross-coupling of amides with boronic acids for the synthesis of ketones by sterically-controlled N-C bond activation is reported. The transformation is characterized by operational simplicity using bench-stable, commercial reagents and catalysts, and a broad substrate scope, including substrates with electron-donating and withdrawing groups on both coupling partners, steric-hindrance, heterocycles, halides, esters and ketones. The scope and limitations are presented in the synthesis of >60 functionalized ketones. Mechanistic studies provide insight into the catalytic cycle of the cross-coupling, including the first experimental evidence for Pd insertion into the amide N-C bond. The synthetic utility is showcased by a gram-scale cross-coupling and cross-coupling at room temperature. Most importantly, this process provides a blueprint for the development of a plethora of metal catalyzed reactions of typically inert amide bonds via acyl-metal intermediates. A unified strategy for amide bond activation to enable metal insertion into N-C amide bond is outlined (Scheme 1).
Effect of Oxime Ether Incorporation in Acyl Indole Derivatives on PPAR Subtype Selectivity
LeNaour, Morgan,Leclerc, Veronique,Farce, Amaury,Caignard, Daniel-Henri,Hennuyer, Nathalie,Staels, Bart,Audinot-Bouchez, Valérie,Boutin, Jean-Albert,Lonchampt, Michel,Dacquet, Catherine,Ktorza, Alain,Berthelot, Pascal,Lebegue, Nicolas
, p. 2179 - 2193 (2013/03/28)
Compounds that simultaneously activate peroxisome proliferator-activated receptor (PPAR) subtypes α and γ have the potential to effectively treat dyslipidemia and type2 diabetes (T2D) in a single pharmaceutically active molecule. The frequently observed side effects of selective PPARγ agonists, such as edema and weight gain, were expected to be overcome by using additive PPARα activity, leading to dual PPARα/γ agonists with balanced activity for both subtypes. Herein we report the discovery, synthesis, and optimization of a new series of α-ethoxyphenylpropionic acid bearing 5- or 6-substituted indoles. The incorporation of oxime ethers on the carbonyl portion of the benzoyl group can bring the PPARα/γ potency ratio equal to or slightly greater than one, as is the case for compounds 20c and 21a. Compound 20c shows high efficacy in an ob/ob mouse model of T2D and dyslipidemia, similar to that of rosiglitazone and tesaglitazar, but with a significant increase in body weight gain. In contrast, compound 21a, less potent as a dual PPARα/γ activator than 20c, showed an interesting pharmacological profile, as it elicits a decrease in body weight relative to reference compounds.
A simple, efficient, and recyclable phosphine-free catalytic system for carbonylative suzuki coupling reaction of aryl and heteroaryl iodides
Qureshi, Ziyauddin S.,Deshmukh, Krishna M.,Tambade, Pawan J.,Bhanage, Bhalchandra M.
experimental part, p. 243 - 250 (2011/03/18)
The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole and 3-iodoquinoline) with various arylboronic acid derivatives providing good to excellent yields of the desired products. The protocol is advantageous due to the ease in handling of the catalyst and simple workup procedure, and environmentally benign with effective catalyst recyclability. Georg Thieme Verlag Stuttgart - New York.
Pd/C: An efficient, heterogeneous and reusable catalyst for phosphane-free carbonylative suzuki coupling reactions of aryl and heteroaryl iodides
Khedkar, Mayur V.,Tambade, Pawan J.,Qureshi, Ziyauddin S.,Bhanage, Bhalchandra M.
experimental part, p. 6981 - 6986 (2011/03/17)
The carbonylative Suzuki coupling reaction of aryl boronic acid with different aryl and heteroaryl iodides was carried out to synthesize various unsymmetrical biaryl ketones by using Pd/C as an efficient, heterogeneous and reusable catalyst. The catalyst exhibits remarkable activity, and its reusability was tested up to four consecutive cycles. The reaction is applicable for various aryl and heteroaryl iodides having different steric and electronic properties. It provides good to excellent yield of the desired products. The developed protocol is advantageous with regard to the ease in handling the catalyst and the simple work-up procedure; it is also an environmentally benign process with effective catalyst recyclability. A facile protocol has been developed for the carbonylative Suzuki coupling reaction of aryl and heteroaryl iodides with Pd/C as effective, heterogeneous, reusable catalyst. The system is applicable for a wide variety of aryl and heteroaryl iodides. Copyright
3-bicycloindole compounds
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, (2008/06/13)
Described herein are compounds selective for a 5-HT1D receptor, which have the general formula:
Synthesis of 5-acylindoles via regioselective acylation of 3-trifluoroacetylindole
Li, Jun,Li, Bogang,Chen, Xiaozhen,Zhang, Guolin
, p. 1447 - 1450 (2007/10/03)
5-Acylindoles were synthesized by regioselective acylation of 3-trifluoroacetylindole with acyl chloride under the catalysis of Lewis acids, followed by hydrolysis of trifluoroacetyl and decarboxylation. Polar solvents were beneficial to the acylation and most of the Lewis acids tested showed good catalytic activities.
New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2, 3 or 5-(α-azolylbenzyl)-1H-indoles
Le Borgne, Marc,Marchand, Pascal,Delevoye-Seiller, Benedicte,Robert, Jean-Michel,Le Baut, Guillaume,Hartmann, Rolf W.,Palzer, Martina
, p. 333 - 336 (2007/10/03)
Six azolyl substituted indoles were synthesized and tested for their activity to inhibit two P450 enzymes: P450 arom and P450 17α. It was observed that the introduction of α-imidazolylbenzyl chain at carbon 3 or 5 on indole nucleus led to very active molecules. Compounds 22, 23 and especially 33 demonstrate very high potential against P450 arom. Under our assay conditions of high substrate concentration the IC50 are 0.057, 0.0785 and 0.041 μM, respectively. These compounds are moderate inhibitors against P450 17α.
Electrophilic substitution of indole on the benzene moiety: A synthesis of 5-acyl- and 5-aroylindoles
Demopoulos, Vassilis J.,Nicolaou, Ioannis
, p. 1519 - 1522 (2007/10/03)
The Vilsmeier-Haack intermediate of indole is acylated, in the presence of a certain excess of AlCl3, exclusively at the benzene ring and especially at position-5. The formed acylindolecarboxaldehydes are readily decarbonylated on heating with Pd/C in mesitylene. Thus, 5-acylindoles and 5- aroylindoles are synthesized in a two step sequence from indole with overall yield of 30-46%.
